Reductive Conversion of Biomass-Derived Furancarboxylic Acids with Retention of Carboxylic Acid Moiety

Abstract

Catalytic reduction systems of 2-furancarboxylic acid (FCA) and 2,5-furandicarboxylic acid (FDCA) with H₂ without reduction of the carboxyl groups are reviewed. FCA and FDCA are produced from furfural and 5-hydroxymethylfurfural which are important platform chemicals in biomass conversions. Furan ring hydrogenation to tetrahydrofuran-2-carboxylic acid (THFCA) and tetrahydrofuran-2,5-dicarboxylic acid (THFDCA) easily proceeds over Pd catalysts. Hydrogenolysis of one C–O bond in the furan ring produces 5-hydroxyvaleric acid (5-HVA) and 2-hydroxyadipic acid. 2-Hydroxyvaleric acid is not produced in the reported systems. 5-HVA can be produced as the lactone form (δ-valerolactone; DVL) or as the esters depending on the solvent. These reactions proceed over Pt catalysts with good yields (~ 70%) at optimized conditions. Hydrogenolysis of two C–O bonds in the furan ring produces valeric acid and adipic acid, the latter of which is a very important chemical in industry and its production from biomass is of high importance. Adipic acid from FDCA can be produced directly over Pt-MoO _x catalyst, indirectly via hydrogenation and hydrodeoxygenation as one-pot reaction using the combination of Pt and acid catalysts such as Pt/niobium oxide, or indirectly via two-step reaction composed of hydrogenation catalyzed by Pd and hydrodeoxygenation catalyzed by iodide ion in acidic conditions. Only the two-step method can give good yield of adipic acid at present.

Keywords

Biomass / Hydrogenolysis / Furanic compound / Carboxylic acid

References

[1] Bozell JJ, Petersen GR Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy’s “Top 10” revisited. Green Chem, 2010, 12(4): 539-554.

[2] Mika LT, Cséfalvay E, Németh Á Catalytic conversion of carbohydrates to initial platform chemicals: chemistry and sustainability. Chem Rev, 2018, 118(2): 505-613.

[3] Millán GG, Hellsten S, Llorca J, et al. Recent advances in the catalytic production of platform chemicals from holocellulosic biomass. ChemCatChem, 2019, 11(8): 2022-2042.

[4] Nakagawa Y, Tamura M, Tomishige K Catalytic reduction of biomass-derived furanic compounds with hydrogen. ACS Catal, 2013, 3(12): 2655-2668.

[5] Caes BR, Teixeira RE, Knapp KG, et al. Biomass to furanics: renewable routes to chemicals and fuels. ACS Sustain Chem Eng, 2015, 3(11): 2591-2605.

[6] Chen S, Wojcieszak R, Dumeignil F, et al. How catalysts and experimental conditions determine the selective hydroconversion of furfural and 5-hydroxymethylfurfural. Chem Rev, 2018, 118(22): 11023-11117.

[7] Paone CXE, Rodríguez-Padrón D, Luque R, et al. Recent catalytic routes for the preparation and the upgrading of biomass derived furfural and 5-hydroxymethylfurfural. Chem Soc Rev, 2020, 49(13): 4273-4306.

[8] Yang ZR, Zhang J, Qian G, et al. Production of biomass derived monomers through catalytic conversion of furfural and hydroxymethylfurfural. Green Chem Eng, 2020, 62(4): 566-606.

[9] Gupta S, Alam MI, Khan TS, et al. Mechanistic approaches toward rational design of a heterogeneous catalyst for ring-opening and deoxygenation of biomass-derived cyclic compounds. ACS Sustain Chem Eng, 2019, 7(12): 10165-10181.

[10] Iriondo A, Agirre I, Viar N, et al. Value-added bio-chemicals commodities from catalytic conversion of biomass derived furan-compounds. Catalysts, 2020, 10(8): 895.

[11] Sajid M, Zhao XB, Liu DH Production of 2,5-furandicarboxylic acid (FDCA) from 5-hydroxymethylfurfural (HMF): recent progress focusing on the chemical-catalytic routes. Green Chem, 2018, 20(24): 5427-5453.

[12] Arias PL, Cecilia JA, Gandarias I, et al. Oxidation of lignocellulosic platform molecules to value-added chemicals using heterogeneous catalytic technologies. Catal Sci Technol, 2020, 10(9): 2721-2757.

[13] Zhou CM, Deng WP, Wan XY, et al. Functionalized carbon nanotubes for biomass conversion: the base-free aerobic oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over platinum supported on a carbon nanotube catalyst. ChemCatChem, 2015, 7(18): 2853-2863.

[14] Chen H, Shen JS, Chen KQ, et al. Atomic layer deposition of Pt nanoparticles on low surface area zirconium oxide for the efficient base-free oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid. Appl Catal A, 2018, 555: 98-107.

[15] Zhou CM, Shi WR, Wan XY, et al. Oxidation of 5-hydroxymethylfurfural over a magnetic iron oxide decorated rGO supporting Pt nanocatalyst. Catal Today, 2019, 330: 92-100.

[16] Gupta NK, Nishimura S, Takagaki A, et al. Hydrotalcite-supported gold-nanoparticle-catalyzed highly efficient base-free aqueous oxidation of 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid under atmospheric oxygen pressure. Green Chem, 2011, 13(4): 824-827.

[17] Wan WY, Zhou CM, Chen JS, et al. Base-free aerobic oxidation of 5-hydroxymethyl-furfural to 2,5-furandicarboxylic acid in water catalyzed by functionalized carbon nanotube-supported Au-Pd alloy nanoparticles. ACS Catal, 2014, 4(7): 2175-2185.

[18] Douthwaite M, Huang X, Iqbal S, et al. The controlled catalytic oxidation of furfural to furoic acid using AuPd/Mg(OH)₂. Catal Sci Technol, 2017, 7(22): 5284-5293.

[19] Ferraz CP, Zieliński M, Pietrowski M, et al. Influence of support basic sites in green oxidation of biobased substrates using Au-promoted catalysts. ACS Sustain Chem Eng, 2018, 6(12): 16332-16340.

[20] Bonincontro D, Lolli A, Villa A, et al. AuPd-nNiO as an effective catalyst for the base-free oxidation of HMF under mild reaction conditions. Green Chem, 2019, 21(15): 4090-4099.

[21] Cai CL, Xu JG, Wang HY, et al. Homogeneous base-free oxidation of 5-hydroxymethyfufural to 2,5-furandicarboxylic acid over Au/Mg(OH)₂ catalysts. ChemistrySelect, 2020, 5(41): 12785-12790.

[22] Pichler CM, Al-Shaal MG, Gu D, et al. Ruthenium supported on high-surface-area zirconia as an efficient catalyst for the base-free oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid. Chemsuschem, 2018, 11(13): 2083-2090.

[23] Zuo XB, Venkitasubramanian P, Busch DH, et al. Optimization of Co/Mn/Br-catalyzed oxidation of 5-hydroxymethylfurfural to enhance 2,5-furandicarboxylic acid yield and minimize substrate burning. ACS Sustain Chem Eng, 2016, 4(7): 3659-3668.

[24] Hayashi E, Komanoya T, Kamata K, et al. Heterogeneously-catalyzed aerobic oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid with MnO₂. Chemsuschem, 2017, 10(4): 654-658.

[25] Hayashi E, Yamaguchi Y, Kamata K, et al. Effect of MnO₂ crystal structure on aerobic oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid. J Am Chem Soc, 2019, 141(2): 890-900.

[26] Sousa AF, Vilela C, Fonseca AC, et al. Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency. Polym Chem, 2015, 6(33): 5961-5983.

[27] Papageorgiou GZ, Papageorgiou DG, Terzopoulou Z, et al. Production of bio-based 2,5-furan dicarboxylate polyesters: recent progress and critical aspects in their synthesis and thermal properties. Eur Polym J, 2016, 83: 202-229.

[28] Loos K, Zhang RY, Pereira I, et al. A perspective on PEF synthesis, properties, and end-life. Front Chem, 2020, 8: 585.

[29] Luneau M, Lim JS, Patel DA, et al. Guidelines to achieving high selectivity for the hydrogenation of α, β-unsaturated aldehydes with bimetallic and dilute alloy catalysts: a review. Chem Rev, 2020, 120(23): 12834-12872.

[30] Maris M, Huck WR, Mallat T, et al. Palladium-catalyzed asymmetric hydrogenation of furan carboxylic acids. J Catal, 2003, 219: 52-58.

[31] Boussie TR, Dias EL, Fresco ZM et al (2010) Production of adipic acid and derivatives from carbohydrate-containing materials. U.S. Patent 0317822

[32] Zaytsev AV, Pickles JE, Harnor SJ Concise syntheses of bridged morpholines. RSC Adv, 2016, 6(59): 53955-53957.

[33] Sun QH, Wang S, Liu HC Selective hydrogenolysis of α-C−O bond in biomass-derived 2-furancarboxylic acid to 5-hydroxyvaleric acid on supported Pt catalysts at near-ambient temperature. ACS Catal, 2019, 9(12): 11413-11425.

[34] Besson M, Pinel C Diastereoselective heterogeneous catalytic hydrogenation of aromatic or heteraromatic compounds. Top Catal, 2003, 25(1–4): 43-61.

[35] Zhang XB, Chen LN, Li YJ, et al. Palladium NPs supported on sulfonic acid functionalized metal–organic frameworks as catalysts for biomass cascade reactions. Dalton Trans, 2019, 48(17): 5515-5519.

[36] Asano T, Takagi H, Nakagawa Y, et al. Selective hydrogenolysis of 2-furancarboxylic acid to 5-hydroxyvaleric acid derivatives over supported platinum catalysts. Green Chem, 2019, 21(22): 6133-6145.

[37] Maris M, Mallat T, Orglmeister E, et al. On the role of modifier structure in the palladium-catalyzed enantioselective hydrogenation of furan-2-carboxylic acid. J Mol Catal A, 2004, 219: 371-376.

[38] Studer M, Wedemeyer-Exl C, Spindler F, et al. Enantioselective homogeneous hydrogenation of monosubstituted pyridines and furans. Monatschefte Chem, 2000, 131: 1335-1343.

[39] Nakagawa Y, Tamura M, Tomishige K Catalytic conversions of furfural to pentanediols. Catal Surv Asia, 2015, 19: 249-256.

[40] Liu SB, Tamura M, Nakagawa Y, et al. Catalytic transformations of furfural and its derived compounds into pentanediols, 2018 Singapore World Scientific 91-109.

[41] Enjamuri N, Darbha S Solid catalysts for conversion of furfural and its derivatives to alkanediols. Catal Rev Sci Eng, 2020, 62(4): 566-606.

[42] Smith HA, Fuzek JF Catalytic hydrogenation of furan and substituted furans on platinum. J Am Chem Soc, 1949, 71(2): 415-419.

[43] Xu WJ, Wang HF, Liu XH, et al. Direct catalytic conversion of furfural to 1,5-pentanediol by hydrogenolysis of the furan ring under mild conditions over Pt/Co₂AlO₄ catalyst. Chem Commun, 2011, 47(13): 3924-3926.

[44] Mizugaki T, Yamakawa T, Nagatsu Y, et al. Direct transformation of furfural to 1,2-pentanediol using a hydrotalcite-supported platinum nanoparticle catalyst. ACS Sustain Chem Eng, 2014, 2(10): 2243-2247.

[45] Ma RF, Wu XP, Tong T, et al. The critical role of water in the ring opening of furfural alcohol to 1,2-pentanediol. ACS Catal, 2017, 7(1): 333-337.

[46] Tong T, Xia QN, Liu XH, et al. Direct hydrogenolysis of biomass-derived furans over Pt/CeO₂ catalyst with high activity and stability. Catal Commun, 2017, 101: 129-133.

[47] Tong T, Liu XH, Guo Y, et al. The critical role of CeO₂ crystal-plane in controlling Pt chemical states on the hydrogenolysis of furfuryl alcohol to 1,2-pentanediol. J Catal, 2018, 365: 420-428.

[48] Yeh JY, Matsagar BM, Chen SS, et al. Synergistic effects of Pt-embedded, MIL-53-derived catalysts (Pt@Al₂O₃) and NaBH₄ for water-mediated hydrogenolysis of biomass-derived furfural to 1,5-pentanediol at near-ambient temperature. J Catal, 2020, 390: 46-56.

[49] Zhu YR, Zhao WF, Zhang J, et al. Selective activation of C-OH, C–O–C, or C=C in furfuryl alcohol by engineered Pt sites supported on layered double oxides. ACS Catal, 2020, 10(15): 8032-8041.

[50] Wei LF, Zhang JX, Deng WP, et al. Catalytic transformation of 2,5-furandicarboxylic acid to adipic acid over niobic acid-supported Pt nanoparticles. Chem Commun, 2019, 55(55): 8013-8016.

[51] Asano T, Tamura M, Nakagawa Y, et al. Selective hydrodeoxygenation of 2-furancarboxylic acid to valeric acid over molybdenum-oxide-modified platinum catalyst. ACS Sustain Chem Eng, 2016, 4(12): 6253-6257.

[52] Asano T, Nakagawa Y, Tamura M, et al. Structure and mechanism of titania-supported platinum–molybdenum catalyst for hydrodeoxygenation of 2-furancarboxylic acid to valeric acid. ACS Sustain Chem Eng, 2019, 7(10): 9601-9612.

[53] Nakagawa Y, Liu SB, Tamura M, et al. Catalytic total hydrodeoxygenation of biomass-derived polyfunctionalized substrates to alkanes. Chemsuschem, 2015, 8(7): 1114-1132.

[54] Luo WH, Cao WX, Bruijnincx PCA, et al. Zeolite-supported metal catalysts for selective hydrodeoxygenation of biomass-derived platform molecules. Green Chem, 2019, 21(14): 3744-3768.

[55] Li XL, Zhai ZJ, Tang CM, et al. Production of propionic acid via hydrodeoxygenation of lactic acid over Fe _xO _y catalysts. RSC Adv, 2016, 6(67): 62252-62262.

[56] Li XL, Pang J, Zhang J, et al. Vapor-phase deoxygenation of lactic acid to biopropionic acid over dispersant-enhanced molybdenum oxide catalyst. Ind Eng Chem Res, 2019, 58(1): 101-109.

[57] Tanabe K Niobic acid as an unusual acidic solid material. Mater Chem Phys, 1987, 17(1–2): 217-225.

[58] Zhu R, Zhou GY, Gong BX, et al. Cascade conversion of furancarboxylic acid to butanediol diacetate over Pd/C and La(OTf)₃ catalytic system. Appl Catal A, 2020, 608: 117888.

[59] Gilkey MJ, Mironenko AV, Vlachos DG, et al. Adipic acid production via metal-free selective hydrogenolysis of biomass-derived tetrahydrofuran-2,5-dicarboxylic acid. ACS Catal, 2017, 7(10): 6619-6634.

[60] Gilkey MJ, Balakumar R, Vlachos DG, et al. Adipic acid production catalyzed by a combination of a solid acid and an iodide salt from biomass-derived tetrahydrofuran-2,5-dicarboxylic acid. Catal Sci Technol, 2018, 8(10): 2661-2671.

[61] Gilkey MJ, Cho HK, Murphy BM, et al. Catalytic adipic acid production on zeolites from biomass-derived tetrahydrofuran-2,5-dicarboxylic acid. ACS Appl Energy Mater, 2020, 3(1): 99-105.

[62] Nakagawa Y, Tomishige K Catalyst development for the hydrogenolysis of biomass-derived chemicals to value-added ones. Catal Surv Asia, 2011, 15: 111-116.

[63] Tomishige K, Nakagawa Y, Tamura M Selective hydrogenolysis and hydrogenation using metal catalysts directly modified with metal oxide species. Green Chem, 2017, 19(13): 2876-2924.

[64] Tomishige K, Nakagawa Y, Tamura M Taming heterogeneous rhenium catalysis for the production of biomass-derived chemicals. Chin Chem Lett, 2020, 31(5): 1071-1077.

[65] Tomishige K, Nakagawa Y, Tamura M Design of supported metal catalysts modified with metal oxides for hydrodeoxygenation of biomass-related molecules. Curr Opin Green Sustain Chem, 2020, 22: 13-21.

[66] Liu LJ, Asano T, Nakagawa Y, et al. One-pot synthesis of 1,3-butanediol by 1,4-anhydroerythritol hydrogenolysis over a tungsten-modified platinum on silica catalyst. Green Chem, 2020, 22(8): 2375-2380.

[67] Aihara T, Miura H, Shishido T Investigation of the mechanism of the selective hydrogenolysis of C-O bonds over a Pt/WO₃/Al₂O₃ catalyst. Catal Today, 2020, 352: 73-79.

[68] Wang J, Yang M, Wang AQ Selective hydrogenolysis of glycerol to 1,3-propanediol over Pt–W based catalysts. Chin J Catal, 2020, 41(9): 1311-1319.

[69] Asano T, Nakagawa Y, Tamura M, et al. Hydrogenolysis of tetrahydrofuran-2-carboxylic acid over tungsten-modified rhodium catalyst. Appl Catal A, 2020, 602: 117723.

[70] Tamura M, Tamura R, Takeda Y, et al. Catalytic hydrogenation of amino acids to amino alcohols with complete retention of configuration. Chem Commun, 2014, 50(50): 6656-6659.

[71] Tamura M, Tamura R, Takeda Y, et al. Insight into the mechanism of hydrogenation of amino acids to amino alcohols catalyzed by a heterogeneous MoO _x-modified Rh catalyst. Chem Eur J, 2014, 21(7): 3097-3107.

[72] Li MX, Li GY, Li N, et al. Aqueous phase hydrogenation of levulinic acid to 1,4-pentanediol. Chem Commun, 2014, 50(12): 1414-1416.

[73] Nakagawa Y, Tamura R, Tamura M, et al. Combination of supported bimetallic rhodium–molybdenum catalyst and cerium oxide for hydrogenation of amide. Sci Technol Adv Mater, 2015, 16: 014901.

[74] Takeda Y, Nakagawa Y, Tomishige K Selective hydrogenation of higher saturated carboxylic acids to alcohols using a ReO _x-Pd/SiO₂ catalyst. Catal Sci Technol, 2012, 2(11): 2221-2223.

[75] Tamura M, Nakagawa Y, Tomishige K Recent developments of heterogeneous catalysts for hydrogenation of carboxylic acids to their corresponding alcohols. Asian J Org Chem, 2020, 9(2): 126-143.

[76] Van de Vyver S, Román-Leshkov Y Emerging catalytic processes for the production of adipic acid. Catal Sci Technol, 2013, 3(6): 1465-1479.

[77] Mahmoudi H, Mahmoudi M, Doustdar O, et al. A review of Fischer Tropsch synthesis process, mechanism, surface chemistry and catalyst formulation. Biofuel Eng, 2017, 2(1): 11-31.

[78] Wang HM, Male J, Wang Y Recent advances in hydrotreating of pyrolysis bio-oil and its oxygen-containing model compounds. ACS Catal, 2013, 3(5): 1047-1070.

[79] Han YL, Gholizadeh M, Tran CC, et al. Hydrotreatment of pyrolysis bio-oil: a review. Fuel Proc Technol, 2019, 195: 106140.

[80] Wang XC, Arai M, Wu QF Hydrodeoxygenation of lignin-derived phenolics: a review on the active sites of supported metal catalysts. Green Chem, 2020, 22(23): 8140-8168.

[81] Nakagawa Y, Ishikawa M, Tamura M, et al. Selective production of cyclohexanol and methanol from guaiacol over Ru catalyst combined with MgO. Green Chem, 2014, 16(4): 2197-2203.

[82] Ishikawa M, Tamura M, Nakagawa Y, et al. Demethoxylation of guaiacol and methoxybenzenes over carbon-supported Ru–Mn catalyst. Appl Catal B, 2016, 182: 193-203.

[83] Li CC, Nakagawa Y, Tamura M, et al. Hydrodeoxygenation of guaiacol to phenol over ceria-supported iron catalysts. ACS Catal, 2020, 10(24): 14624-14639.

[84] Skoog E, Shin JH, Saez-Jimenez V, et al. Biobased adipic acid - the challenge of developing the production host. Biotechnol Adv, 2018, 36(8): 2248-2263.

[85] Shiramizu M, Toste FD Expanding the scope of biomass-derived chemicals through tandem reactions based on oxorhenium-catalyzed deoxydehydration. Angew Chem Int Ed, 2013, 52(49): 12905-12909.

[86] Li XK, Wu D, Lu T, et al. Highly efficient chemical process to convert mucic acid into adipic acid and DFT studies of the mechanism of the rhenium-catalyzed deoxydehydration. Angew Chem Int Ed, 2014, 53(16): 4200-4204.

[87] Zhang HF, Li XK, Su XY, et al. Production of adipic acid from sugar beet residue by combined biological and chemical catalysis. ChemCatChem, 2016, 8(8): 1500-1506.

[88] Shin N, Kwon S, Moon S, et al. Ionic liquid-mediated deoxydehydration reactions: green synthetic process for bio-based adipic acid. Tetrahedron, 2017, 73(32): 4758-4765.

[89] Larson RT, Samant A, Chen JB, et al. Hydrogen gas-mediated deoxydehydration/hydrogenation of sugar acids: catalytic conversion of glucarates to adipates. J Am Chem Soc, 2017, 139(40): 14001-14004.

[90] Lin JC, Song HY, Shen XR, et al. Zirconia-supported rhenium oxide as an efficient catalyst for the synthesis of biomass-based adipic acid ester. Chem Commun, 2019, 55(74): 11017-11020.

[91] Shi HX, Zhang LF, Wu YD, et al. Production of adipic acid derivatives from D-glucaric acid by hydrodeoxygenation mediated with hydroiodic acid. Catal Lett, 2020, 151(2): 338-343.

[92] Wang Y, Deng WP, Yan LF, et al. Efficient catalysts for green synthesis of adipic acid from biomass. Angew Chem Int Ed, 2020, 60(9): 4712-4719.

[93] Meessen P, Vogt D, Keim W Highly regioselective hydroformylation of internal, functionalized olefins applying Pt/Sn complexes with large bite angle diphosphines. J Organomet Chem, 1998, 551(1–2): 165-170.

[94] Wu DD, Chen Z, Jia ZB, et al. Synthesis of dimethyl adipate from cyclopentanone and dimethyl carbonate over solid base catalysts. Sci Chin Chem, 2012, 55(3): 380-385.

[95] Nobbs JD, Zainal NZB, Tan J, et al. Bio-based pentenoic acids as intermediates to higher value-added mono- and dicarboxylic acids. ChemistrySelect, 2016, 1(3): 539-544.

[96] Marckwordt A, El Ouahabi F, Amani H, et al. Nylon intermediates from bio-based levulinic acid. Angew Chem Int Ed, 2019, 58(11): 3486-3490.

[97] Obara N, Hirasawa S, Tamura M, et al. Oxidative cleavage of vicinal diols with the combination of platinum and vanadium catalysts and molecular oxygen. ChemCatChem, 2016, 8(9): 1732-1738.

[98] Nakagawa Y, Sekine D, Obara N, et al. Oxidative C-C cleavage of ketols over vanadium-carbon catalysts. ChemCatChem, 2017, 9(17): 3412-3419.

[99] Hatakeyama K, Nakagawa Y, Tamura M, et al. Efficient production of adipic acid from 2-methoxycyclohexanone by aerobic oxidation with a phosphotungstic acid catalyst. Green Chem, 2020, 22(15): 4962-4974.

[100] Rogers O, Pattisson S, Engel RV, et al. Adipic acid formation from cyclohexanediol using platinum and vanadium catalysts: elucidating the role of homogeneous vanadium species. Catal Sci Technol, 2020, 10(13): 4210-4218.

[101] Duale K, Zięba M, Chaber P, et al. Molecular level structure of biodegradable poly(delta-valerolactone) obtained in the presence of boric acid. Molecules, 2018, 23(8): 2034.

[102] Pinkos R, Bauduin C, Paul A et al (2011) Process for preparing delta-valerolactone in the gas phase. U.S. Patent 0 237 806

[103] Adkins H, Billica HR The hydrogenation of esters to alcohols at 25–150°. J Am Chem Soc, 1948, 70(9): 3121-3125.

[104] Mock GH (1981) Process for preparing adipic acid with recovery of glutaric acid and succinic acids. U.S. Patent 4 254 283

[105] ten Brink GJ, Arends IWCE, Sheldon RA The Baeyer-Villiger reaction: new developments toward greener procedures. Chem Rev, 2004, 104(9): 4105-4124.

[106] Hara T, Hatakeyama M, Kim A, et al. Preparation of clay-supported Sn catalysts and application to Baeyer–Villiger oxidation. Green Chem, 2012, 14(3): 771-777.

[107] Saikia PK, Sarmah PP, Borah BJ, et al. Stabilized Fe₃O₄ magnetic nanoparticles into nanopores of modified montmorillonite clay: a highly efficient catalyst for the Baeyer-Villiger oxidation under solvent free conditions. Green Chem, 2016, 18(9): 2843-2850.

[108] Xing C, Tan R, Hao PB, et al. Graphene oxide supported chlorostannate (IV) ionic liquid: Brønsted–Lewis acidic combined catalyst for highly efficient Baeyer–Villiger oxidation in water. Mol Catal, 2017, 433: 37-47.

[109] Verrier C, Moebs-Sanchez S, Queneau Y, et al. The Piancatelli reaction and its variants: recent applications to high added-value chemicals and biomass valorization. Org Biomol Chem, 2018, 16(5): 676-687.

[110] Lange JP, Price R, Ayoub PM, et al. Valeric biofuels: a platform of cellulosic transportation fuels. Angew Chem Int Ed, 2010, 49(26): 4479-4483.

[111] Yu ZH, Lu XB, Xiong J, et al. Transformation of levulinic acid to valeric biofuels: a review on heterogeneous bifunctional catalytic systems. Chemsuschem, 2019, 12(17): 3915-3930.

[112] Weng RG, Yu ZH, Xiong J, et al. Effects of water in the heterogeneous catalytic valorization of levulinic acid into γ-valerolactone and its derivative. Green Chem, 2020, 22(10): 3013-3027.

[113] Rackemann DW, Doherty WOS The conversion of lignocellulosics to levulinic acid. Biofuel Bioprod Biorefin, 2011, 5(2): 198-214.

[114] Pileidis FD, Titirici MM Levulinic acid biorefineries: new challenges for efficient utilization of biomass. Chemsuschem, 2016, 9(6): 562-582.

[115] Karanwal N, Verma D, Butolia P, et al. One-pot direct conversion of levulinic acid into high-yield valeric acid over a highly stable bimetallic Nb-Cu/Zr-doped porous silica catalyst. Green Chem, 2020, 22(3): 766-787.